(+/-)-3,8a,3',8'a-tetramethyl-5,5'-dimethylene-4,4a,5,6,7,8,8a,9,4',4'a,5',6',7',8',8'a,9'-hexadecahydro-[9a,9'a]bi[naphtho[2,3-b]furanyl]-2,2'-dione

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+/-)-3,8a,3',8'a-tetramethyl-5,5'-dimethylene-4,4a,5,6,7,8,8a,9,4',4'a,5',6',7',8',8'a,9'-hexadecahydro-[9a,9'a]bi[naphtho[2,3-b]furanyl]-2,2'-dione
• 英文别名: 3,8a,3',8'a-tetramethyl-5,5'-dimethylene-4,4a,5,6,7,8,8a,9,4',4'a,5',6',7',8',8'a,9'-hexadecahydro[9a,9'a]bi[naphtho[2,3-b]furanyl]-2,2'-dione；rac-biepiasterolide；(+/-)-biepiasterolide；Biepiasterolide；(4aR,8aS,9aS)-9a-[(4aR,8aS,9aS)-3,8a-dimethyl-5-methylidene-2-oxo-4,4a,6,7,8,9-hexahydrobenzo[f][1]benzofuran-9a-yl]-3,8a-dimethyl-5-methylidene-4,4a,6,7,8,9-hexahydrobenzo[f][1]benzofuran-2-one
• 化学式: C₃₀H₃₈O₄
• 分子量: 462.629
• InChiKey: RBJDJJGMGHKQMI-FLCAQCBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  34
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苍术酮 在 吡啶 、 氯化亚砜 、 cobalt,triphenylphosphane,chloride 、 air 、 (+/-)-atractylenolide 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 842.5h， 生成 (+/-)-3,8a,3',8'a-tetramethyl-5,5'-dimethylene-4,4a,5,6,7,8,8a,9,4',4'a,5',6',7',8',8'a,9'-hexadecahydro-[9a,9'a]bi[naphtho[2,3-b]furanyl]-2,2'-dione
  参考文献：
  名称：

  Dimerization of Butenolide Structures. A Biomimetic Approach to the Dimeric Sesquiterpene Lactones (±)-Biatractylolide and (±)-Biepiasterolide

  摘要：

  The biomimetic synthesis of the bisesquiterpene lactones (+/-)-biatractylolide 1 and (+/-)-biepiasterolide 2 via dimerization of the captodative stabilized radical 8 is reported. Atractylon 7 has also been shown to be a possible intermediate during the biosynthesis of biatractylolide 1, biepiasterolide 2, atractylolide 3, and hydroxyatractylolide 4.

  DOI：

  10.1021/jo0488053

文献信息

• Regioselectivity of dimerisation of butenolides via captodative stabilised radicaloid intermediates
  作者：Sharanjeet K. Bagal、Robert M. Adlington、Rohan A.B. Brown、Jack E. Baldwin

  DOI：10.1016/j.tetlet.2005.04.125

  日期：2005.7

  The regioselective outcome observed during dimerisation of butenolides to dimeric structures via captodative stabilised radicaloids has been studied. The captodative stabilised radicaloids were generated by initial conversion of butenolides to chlorobutenolides via the corresponding hydroxybutenolides, followed by treatment with CoCl(PPh3)3.

  研究了在丁烯内酯通过capdodative稳定的基团二聚化为二聚体结构过程中观察到的区域选择性结果。通过将丁烯内酯通过相应的羟基丁烯内酯初步转化为氯丁烯内酯，然后用CoCl（PPh 3）3处理，生成了具有captodative稳定性的自由基。
• Biomimetic Synthesis of Biatractylolide and Biepiasterolide
  作者：Sharanjeet K. Bagal、Robert M. Adlington、Jack E. Baldwin、Rodolfo Marquez、Andrew Cowley

  DOI：10.1021/ol035022f

  日期：2003.8.1

  graphicThe biomimetic synthesis of the bisesquiterpenoids biatractylolide 1 and bieplasterolide 2 is reported.
• Dimerization of Butenolide Structures. A Biomimetic Approach to the Dimeric Sesquiterpene Lactones (±)-Biatractylolide and (±)-Biepiasterolide
  作者：Sharanjeet K. Bagal、Robert M. Adlington、Jack E. Baldwin、Rodolfo Marquez

  DOI：10.1021/jo0488053

  日期：2004.12.1

  The biomimetic synthesis of the bisesquiterpene lactones (+/-)-biatractylolide 1 and (+/-)-biepiasterolide 2 via dimerization of the captodative stabilized radical 8 is reported. Atractylon 7 has also been shown to be a possible intermediate during the biosynthesis of biatractylolide 1, biepiasterolide 2, atractylolide 3, and hydroxyatractylolide 4.